Carfenazine

Carfenazine (INN) (former developmental code name WY-2445), or carphenazine (BAN), also known as carphenazine maleate (USAN) (brand name Proketazine; former developmental code name NSC-71755), is an antipsychotic and tranquilizer of the phenothiazine group that was withdrawn from the market.[1][2][3]

Carfenazine
Clinical data
Other namesProketazine, Carphenazin
License data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • Withdrawn
Identifiers
IUPAC name
  • 1-(10-{3-[4-(2-Hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)propan-1-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.018.249
Chemical and physical data
FormulaC24H31N3O2S
Molar mass425.59 g·mol−1
3D model (JSmol)
SMILES
  • CCC(=O)c1ccc2Sc3ccccc3N(CCCN4CCN(CCO)CC4)c2c1
InChI
  • InChI=1S/C24H31N3O2S/c1-2-22(29)19-8-9-24-21(18-19)27(20-6-3-4-7-23(20)30-24)11-5-10-25-12-14-26(15-13-25)16-17-28/h3-4,6-9,18,28H,2,5,10-17H2,1H3
  • Key:XZSMZRXAEFNJCU-UHFFFAOYSA-N

Synthesis
Thieme Synthesis:[4] Patent:[5][6]

The alkylation reaction between 2-Propionyl Phenothiazine [92-33-1] (1) and 1-Bromo-3-chloropropane (2) gives 1-[10-(3-chloropropyl)phenothiazin-2-yl]propan-1-one [95157-45-2] (3). A second alkylation step, this time with 2-(1-Piperazinyl)ethanol [103-76-4] (4) completes the synthesis of Carfenazine (5).

NB: Although above procedure is proof-of-concept, bear in mind no protecting group {Other patent uses ketalization technique}

Analogues

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 224–. ISBN 978-1-4757-2085-3.
  2. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 862–. ISBN 978-0-8155-1856-3.
  3. Briggs GG, Freeman RK, Yaffe SJ (2011). Drugs in Pregnancy and Lactation: A Reference Guide to Fetal and Neonatal Risk. Lippincott Williams & Wilkins. pp. 213–. ISBN 978-1-60831-708-0.
  4. Zhuraulev, S.V. et al, Zh. Obshch. Khim., 1962, 32, 2244
  5. M. H. Sherlock, N. Sperber, U.S. Patent 2,985,654 (1961 to Schering)
  6. R. F. Tislow et al., U.S. Patent 3,023,146 (1962 to American Home Products).



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